TIGER

Experimental Design and Optimization: Application to a Grignard ReactionNaoual Bouzidi and Christel GozziThis 5-week project, which systematically investigates optimizing the synthesis of benzyl-1-cyclopentan-1-ol, constitutes an initiation into research methodology and experimental design to prepare the student-engineer for an industry internship. Other pedagogical goals include experience in synthetic techniques, obtaining reproducible yields, and using quantitative analysis methods.Bouzidi, Naoual; Gozzi, Christel. J. Chem. Educ.2008, 85, 1544.

Addition Reactions |

Alcohols |

Aldehydes / Ketones |

Chemometrics |

Gas Chromatography |

Organometallics |

Synthesis

Evaluating Mechanisms of Dihydroxylation by Thin-Layer ChromatographyBenjamin T. Burlingham and Joseph C. RettigPresents a microscale experiment in which cyclohexene is dihydroxylated under three sets of conditions and the products determined through thin-layer chromatography. Teams of students evaluate proposed mechanisms for each dihydroxylation in light of the data collected.Burlingham, Benjamin T.; Rettig, Joseph C. J. Chem. Educ.2008, 85, 959.

Addition Reactions |

Alkenes |

Diastereomers |

Mechanisms of Reactions |

Microscale Lab |

Stereochemistry |

Synthesis |

Thin Layer Chromatography

Regioselectivity in Organic Synthesis: Preparation of the Bromohydrin of α-MethylstyreneBrad Andersh, Kathryn N. Kilby, Meghan E. Turnis, and Drew L. MurphyIn the described experiment, the regiochemical outcome of the addition of "HOBr" to a-methylstyrene is investigated. Although both "classic" qualitative analysis and instrumental techniques are described, the emphasis of this experiment is on the utilization 13C and DEPT-135 NMR spectroscopy to determine the regiochemical outcome of the addition. Andersh, Brad; Kilby, Kathryn N.; Turnis, Meghan E.; Murphy, Drew L. J. Chem. Educ.2008, 85, 102.

Addition Reactions |

Alcohols |

Alkenes |

Constitutional Isomers |

IR Spectroscopy |

Microscale Lab |

NMR Spectroscopy |

Synthesis

Reaction-Map of Organic ChemistrySteven MurovThe Reaction-Map of Organic Chemistry has been designed to provide an overview of most of the reactions needed for the organic chemistry course and should help students develop synthetic routes from one functional group to another.Murov, Steven. J. Chem. Educ.2007, 84, 1224.

Addition Reactions |

Electrophilic Substitution |

Elimination Reactions |

Nucleophilic Substitution |

Oxidation / Reduction |

Periodicity / Periodic Table |

Reactions |

Synthesis |

Enrichment / Review Materials

The Aldol Addition and Condensation: The Effect of Conditions on Reaction PathwayR. David Crouch, Amie Richardson, Jessica L. Howard, Rebecca L. Harker, and Kathryn H. BarkerDescribes an experiment offering the opportunity for students to observe the critical role that reaction temperature and base strength have in determining the product of the base-mediated addition of a ketone to an aldehyde.Crouch, R. David; Richardson, Amie; Howard, Jessica L.; Harker, Rebecca L.; Barker, Kathryn H. J. Chem. Educ.2007, 84, 475.

Diels–Alder Synthesis of endo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximideMarsha R. Baar and Kristin Wustholzendo-cis-N-Phenylbicyclo[2.2.2]oct-5-en-2,3-dicarboximide was synthesized by a DielsAlder cycloaddition of 1,3-cyclohexadiene and N-phenylmaleimide in ethyl acetate. 1,3-Cyclohexadiene and N-phenylmaleimide were selected to illustrate the Alder rule, which reflects a preference for endo products and to overcome the difficulties associated with the traditional combination of 1,3-cyclopentadiene and maleic anhydride. Baar, Marsha R.; Wustholz, Kristin. J. Chem. Educ.2005, 82, 1393.

Asymmetric Synthesis |

Microscale Lab |

Stereochemistry |

Addition Reactions |

Alkenes |

IR Spectroscopy |

NMR Spectroscopy

The Evolution of a Green Chemistry Laboratory Experiment: Greener Brominations of StilbeneLallie C. McKenzie, Lauren M. Huffman, and James E. HutchisonWe describe two new greener alkene bromination reactions that offer enhanced laboratory safety and convey important green chemistry concepts, in addition to illustrating the chemistry of alkenes. The two alternative reactions, one involving pyridinium tribromide and a second using hydrogen peroxide and hydrobromic acid, are compared to the traditional bromination of stilbene through the application of green metrics, including atom economy, percent experimental atom economy, E factor, and effective mass yield.McKenzie, Lallie C.; Huffman, Lauren M.; Hutchison, James E. J. Chem. Educ.2005, 82, 306.

Synthesis |

Green Chemistry |

Aromatic Compounds |

Addition Reactions |

Alkenes

The Sharpless Asymmetric Dihydroxylation in the Organic Chemistry Majors LaboratoryChristopher J. Nichols and Melissa R. TaylorA six-period laboratory exercise has been developed that uses the convenient Sharpless asymmetric dihydroxylation (AD) to illustrate the principles of a chiral synthesis. Using one particular alkene, students perform a racemic dihydroxylation, an AD using a commercially available AD-mix, and then an AD using an ester derivative of dihydroquinidine that they synthesized themselves. The structures of the products are confirmed with 1H NMR spectroscopy and the enantiomeric excesses of the diols are determined using a chiral GC column. Nichols, Christopher J.; Taylor, Melissa R. J. Chem. Educ.2005, 82, 105.

A -78°C Sequential Michael Addition for the Organic LabMichael W. TanisThis paper introduces a cold-temperature enolate alkylation reaction that can be performed safely and inexpensively by undergraduate students in approximately two 3-hour lab sessions. Tanis, Michael W. J. Chem. Educ.1997, 74, 112.